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McCutcheon played high school football at Bishop Amat Memorial High School in La Puente, California under the direction of then Head Coach, Mark Paredes. As a senior, he rushed for 2,456 yards in 1994; however he chose to play cornerback in college because his pro prospects were considered better at that position.[1]

McCutcheon was named the New York Jets' assistant defensive backs coach on January 29, 2015.[5] On January 16, 2018, it was announced that McCutcheon would not be retained as the assistant defensive backs coach for the 2018 season.[6]